# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_130927_dnfofh_0m
_database_code_depnum_ccdc_archive 'CCDC 1028788'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H4 N16 O22'
_chemical_formula_weight         724.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.974(3)
_cell_length_b                   14.968(3)
_cell_length_c                   11.822(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.260(3)
_cell_angle_gamma                90.00
_cell_volume                     2615.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7959
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.32
_reflns_number_total             5327
_reflns_number_gt                4668
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0834P)²+1.0604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(11)
_refine_ls_number_reflns         5327
_refine_ls_number_parameters     468
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3974(2) 0.4738(2) 0.7036(3) 0.0480(7) Uani 1 1 d . . .
C2 C 0.41655(19) 0.56159(19) 0.6561(2) 0.0427(6) Uani 1 1 d . . .
C3 C 0.49733(19) 0.60396(17) 0.6374(2) 0.0403(6) Uani 1 1 d . . .
C4 C 0.65454(19) 0.60189(16) 0.6349(2) 0.0378(5) Uani 1 1 d . . .
C5 C 0.73982(18) 0.55792(18) 0.6534(2) 0.0394(5) Uani 1 1 d . . .
C6 C 0.76812(18) 0.47074(19) 0.7055(3) 0.0459(6) Uani 1 1 d . . .
C7 C 0.05070(19) 0.35045(18) 0.4476(2) 0.0414(6) Uani 1 1 d . . .
C8 C 0.1350(2) 0.37395(17) 0.4060(2) 0.0401(6) Uani 1 1 d . . .
C9 C 0.17601(18) 0.45684(17) 0.3886(3) 0.0403(6) Uani 1 1 d . . .
C10 C 0.17571(17) 0.61482(17) 0.3887(2) 0.0384(5) Uani 1 1 d . . .
C11 C 0.13669(19) 0.69791(17) 0.4123(2) 0.0419(6) Uani 1 1 d . . .
C12 C 0.0595(2) 0.72174(19) 0.4697(3) 0.0461(6) Uani 1 1 d . . .
O1 O 0.3406(3) 0.3510(3) 0.5949(4) 0.1266(16) Uani 1 1 d . . .
O2 O 0.4659(3) 0.3999(2) 0.5700(4) 0.1033(14) Uani 1 1 d . . .
O3 O 0.4754(3) 0.3713(3) 0.8268(4) 0.1247(17) Uani 1 1 d . . .
O4 O 0.4910(3) 0.5103(3) 0.8679(3) 0.1055(12) Uani 1 1 d . . .
O5 O 0.38644(18) 0.68730(18) 0.5741(3) 0.0723(8) Uani 1 1 d . . .
O6 O 0.57957(13) 0.56668(13) 0.66739(19) 0.0463(5) Uani 1 1 d . . .
O7 O 0.75045(16) 0.68231(16) 0.5713(2) 0.0621(6) Uani 1 1 d . . .
O8 O 0.65635(19) 0.40537(19) 0.5735(3) 0.0821(9) Uani 1 1 d . . .
O9 O 0.7690(3) 0.5207(3) 0.8887(3) 0.1041(12) Uani 1 1 d . . .
O10 O 0.6890(4) 0.4068(3) 0.8409(4) 0.1320(18) Uani 1 1 d . . .
O11 O 0.7661(3) 0.3245(2) 0.6450(6) 0.155(3) Uani 1 1 d . . .
O12 O -0.09387(19) 0.3246(2) 0.3511(3) 0.0805(9) Uani 1 1 d . . .
O13 O -0.02846(16) 0.44732(15) 0.3149(2) 0.0623(7) Uani 1 1 d . . .
O14 O -0.0327(2) 0.4156(3) 0.5765(3) 0.1007(12) Uani 1 1 d . . .
O15 O 0.1116(2) 0.4086(3) 0.6219(3) 0.0893(10) Uani 1 1 d . . .
O16 O 0.25678(17) 0.35323(15) 0.3387(2) 0.0635(6) Uani 1 1 d . . .
O17 O 0.14092(14) 0.53608(12) 0.4158(2) 0.0479(5) Uani 1 1 d . . .
O18 O 0.24887(18) 0.71757(16) 0.3252(2) 0.0654(7) Uani 1 1 d . . .
O19 O 0.1247(2) 0.6296(2) 0.6188(2) 0.0830(9) Uani 1 1 d . . .
O20 O 0.0152(3) 0.7135(3) 0.6475(3) 0.1182(16) Uani 1 1 d . . .
O21 O -0.0603(3) 0.6226(3) 0.4284(6) 0.142(2) Uani 1 1 d . . .
O22 O -0.0536(4) 0.7293(8) 0.3204(5) 0.227(5) Uani 1 1 d . . .
N1 N 0.4027(2) 0.39995(19) 0.6166(3) 0.0619(7) Uani 1 1 d . . .
N2 N 0.4619(2) 0.4498(2) 0.8091(3) 0.0616(7) Uani 1 1 d . . .
N3 N 0.3492(2) 0.6142(2) 0.6167(3) 0.0622(8) Uani 1 1 d . . .
N4 N 0.48009(19) 0.68034(18) 0.5887(3) 0.0552(7) Uani 1 1 d . . .
N5 N 0.66008(19) 0.67777(17) 0.5847(2) 0.0517(6) Uani 1 1 d . . .
N6 N 0.79732(18) 0.6087(2) 0.6134(2) 0.0545(7) Uani 1 1 d . . .
N7 N 0.7263(2) 0.39345(18) 0.6346(3) 0.0612(8) Uani 1 1 d . . .
N8 N 0.7397(2) 0.46438(19) 0.8231(3) 0.0600(7) Uani 1 1 d . . .
N9 N -0.0277(2) 0.6888(3) 0.3997(3) 0.0710(9) Uani 1 1 d . . .
N10 N 0.0660(2) 0.68304(18) 0.5877(3) 0.0566(7) Uani 1 1 d . . .
N11 N 0.1829(2) 0.76033(18) 0.3716(3) 0.0636(8) Uani 1 1 d . . .
N12 N 0.24377(17) 0.62552(17) 0.3363(2) 0.0490(6) Uani 1 1 d . . .
N13 N 0.25019(19) 0.44560(18) 0.3482(3) 0.0559(7) Uani 1 1 d . . .
N14 N 0.18545(19) 0.31109(16) 0.3741(2) 0.0528(6) Uani 1 1 d . . .
N15 N -0.03226(17) 0.37718(16) 0.3630(2) 0.0484(6) Uani 1 1 d . . .
N16 N 0.0426(2) 0.39662(18) 0.5590(2) 0.0528(6) Uani 1 1 d . . .
H1 H 0.834(2) 0.464(2) 0.713(3) 0.046(9) Uiso 1 1 d . . .
H2 H 0.347(3) 0.469(2) 0.720(3) 0.043(9) Uiso 1 1 d . . .
H3 H 0.062(2) 0.786(2) 0.482(3) 0.052(9) Uiso 1 1 d . . .
H4 H 0.056(3) 0.289(3) 0.460(4) 0.069(12) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.475(4) . ?
C1 N2 1.493(5) . ?
C1 N1 1.521(5) . ?
C1 H2 0.82(4) . ?
C2 N3 1.305(4) . ?
C2 C3 1.414(4) . ?
C3 N4 1.287(4) . ?
C3 O6 1.347(3) . ?
C4 N5 1.291(3) . ?
C4 O6 1.351(3) . ?
C4 C5 1.422(4) . ?
C5 N6 1.294(4) . ?
C5 C6 1.476(4) . ?
C6 N7 1.505(4) . ?
C6 N8 1.520(5) . ?
C6 H1 0.98(4) . ?
C7 C8 1.469(4) . ?
C7 N16 1.509(4) . ?
C7 N15 1.518(4) . ?
C7 H4 0.94(4) . ?
C8 N14 1.300(4) . ?
C8 C9 1.414(4) . ?
C9 N13 1.288(4) . ?
C9 O17 1.357(3) . ?
C10 N12 1.285(4) . ?
C10 O17 1.348(3) . ?
C10 C11 1.421(4) . ?
C11 N11 1.300(4) . ?
C11 C12 1.475(4) . ?
C12 N10 1.500(4) . ?
C12 N9 1.511(5) . ?
C12 H3 0.98(4) . ?
O1 N1 1.178(4) . ?
O2 N1 1.168(4) . ?
O3 N2 1.205(5) . ?
O4 N2 1.182(5) . ?
O5 N3 1.361(4) . ?
O5 N4 1.389(4) . ?
O7 N6 1.357(4) . ?
O7 N5 1.389(4) . ?
O8 N7 1.186(4) . ?
O9 N8 1.181(5) . ?
O10 N8 1.189(5) . ?
O11 N7 1.189(4) . ?
O12 N15 1.203(3) . ?
O13 N15 1.200(3) . ?
O14 N16 1.212(4) . ?
O15 N16 1.187(4) . ?
O16 N14 1.363(4) . ?
O16 N13 1.392(4) . ?
O18 N11 1.364(4) . ?
O18 N12 1.387(4) . ?
O19 N10 1.201(4) . ?
O20 N10 1.208(4) . ?
O21 N9 1.179(6) . ?
O22 N9 1.132(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N2 113.2(3) . . ?
C2 C1 N1 110.8(2) . . ?
N2 C1 N1 107.0(3) . . ?
C2 C1 H2 115(2) . . ?
N2 C1 H2 106(2) . . ?
N1 C1 H2 104(2) . . ?
N3 C2 C3 107.8(3) . . ?
N3 C2 C1 119.1(3) . . ?
C3 C2 C1 133.0(2) . . ?
N4 C3 O6 126.5(3) . . ?
N4 C3 C2 110.7(2) . . ?
O6 C3 C2 122.8(2) . . ?
N5 C4 O6 126.3(3) . . ?
N5 C4 C5 110.8(2) . . ?
O6 C4 C5 122.9(2) . . ?
N6 C5 C4 107.8(3) . . ?
N6 C5 C6 120.6(3) . . ?
C4 C5 C6 131.6(2) . . ?
C5 C6 N7 112.4(2) . . ?
C5 C6 N8 109.5(2) . . ?
N7 C6 N8 108.0(3) . . ?
C5 C6 H1 110.0(19) . . ?
N7 C6 H1 107.4(19) . . ?
N8 C6 H1 110(2) . . ?
C8 C7 N16 112.1(2) . . ?
C8 C7 N15 111.9(2) . . ?
N16 C7 N15 106.3(2) . . ?
C8 C7 H4 103(3) . . ?
N16 C7 H4 109(3) . . ?
N15 C7 H4 114(3) . . ?
N14 C8 C9 107.9(3) . . ?
N14 C8 C7 119.6(2) . . ?
C9 C8 C7 132.5(2) . . ?
N13 C9 O17 126.3(2) . . ?
N13 C9 C8 111.1(2) . . ?
O17 C9 C8 122.6(2) . . ?
N12 C10 O17 126.2(3) . . ?
N12 C10 C11 111.6(2) . . ?
O17 C10 C11 122.1(2) . . ?
N11 C11 C10 107.2(3) . . ?
N11 C11 C12 120.0(3) . . ?
C10 C11 C12 132.8(2) . . ?
C11 C12 N10 113.4(3) . . ?
C11 C12 N9 109.9(2) . . ?
N10 C12 N9 107.7(3) . . ?
C11 C12 H3 107(2) . . ?
N10 C12 H3 104(2) . . ?
N9 C12 H3 114(2) . . ?
N3 O5 N4 111.1(2) . . ?
C3 O6 C4 122.0(2) . . ?
N6 O7 N5 112.0(2) . . ?
N14 O16 N13 111.4(2) . . ?
C10 O17 C9 121.9(2) . . ?
N11 O18 N12 112.0(2) . . ?
O2 N1 O1 124.6(4) . . ?
O2 N1 C1 116.9(3) . . ?
O1 N1 C1 118.3(4) . . ?
O4 N2 O3 127.5(4) . . ?
O4 N2 C1 115.8(3) . . ?
O3 N2 C1 116.7(3) . . ?
C2 N3 O5 106.1(3) . . ?
C3 N4 O5 104.4(2) . . ?
C4 N5 O7 103.4(2) . . ?
C5 N6 O7 106.0(3) . . ?
O8 N7 O11 125.0(4) . . ?
O8 N7 C6 118.1(3) . . ?
O11 N7 C6 116.9(3) . . ?
O9 N8 O10 125.5(4) . . ?
O9 N8 C6 115.3(3) . . ?
O10 N8 C6 119.2(4) . . ?
O22 N9 O21 125.9(5) . . ?
O22 N9 C12 115.5(5) . . ?
O21 N9 C12 118.6(4) . . ?
O19 N10 O20 124.8(3) . . ?
O19 N10 C12 118.5(3) . . ?
O20 N10 C12 116.5(3) . . ?
C11 N11 O18 105.9(2) . . ?
C10 N12 O18 103.2(2) . . ?
C9 N13 O16 103.7(2) . . ?
C8 N14 O16 105.9(2) . . ?
O13 N15 O12 127.6(3) . . ?
O13 N15 C7 116.5(2) . . ?
O12 N15 C7 115.8(3) . . ?
O15 N16 O14 126.7(3) . . ?
O15 N16 C7 115.6(3) . . ?
O14 N16 C7 117.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 N3 -139.5(3) . . . . ?
N1 C1 C2 N3 100.3(4) . . . . ?
N2 C1 C2 C3 43.9(5) . . . . ?
N1 C1 C2 C3 -76.4(4) . . . . ?
N3 C2 C3 N4 0.4(4) . . . . ?
C1 C2 C3 N4 177.3(3) . . . . ?
N3 C2 C3 O6 -179.4(3) . . . . ?
C1 C2 C3 O6 -2.4(5) . . . . ?
N5 C4 C5 N6 0.0(3) . . . . ?
O6 C4 C5 N6 -179.8(3) . . . . ?
N5 C4 C5 C6 -179.2(3) . . . . ?
O6 C4 C5 C6 1.0(5) . . . . ?
N6 C5 C6 N7 -111.8(3) . . . . ?
C4 C5 C6 N7 67.4(4) . . . . ?
N6 C5 C6 N8 128.2(3) . . . . ?
C4 C5 C6 N8 -52.6(4) . . . . ?
N16 C7 C8 N14 131.2(3) . . . . ?
N15 C7 C8 N14 -109.4(3) . . . . ?
N16 C7 C8 C9 -50.8(4) . . . . ?
N15 C7 C8 C9 68.6(4) . . . . ?
N14 C8 C9 N13 -0.7(3) . . . . ?
C7 C8 C9 N13 -178.8(3) . . . . ?
N14 C8 C9 O17 -178.6(3) . . . . ?
C7 C8 C9 O17 3.3(5) . . . . ?
N12 C10 C11 N11 0.5(3) . . . . ?
O17 C10 C11 N11 -177.2(3) . . . . ?
N12 C10 C11 C12 -179.7(3) . . . . ?
O17 C10 C11 C12 2.6(5) . . . . ?
N11 C11 C12 N10 -125.8(3) . . . . ?
C10 C11 C12 N10 54.4(4) . . . . ?
N11 C11 C12 N9 113.6(3) . . . . ?
C10 C11 C12 N9 -66.2(4) . . . . ?
N4 C3 O6 C4 -9.1(5) . . . . ?
C2 C3 O6 C4 170.6(2) . . . . ?
N5 C4 O6 C3 8.3(4) . . . . ?
C5 C4 O6 C3 -172.0(3) . . . . ?
N12 C10 O17 C9 -0.2(4) . . . . ?
C11 C10 O17 C9 177.1(3) . . . . ?
N13 C9 O17 C10 8.9(5) . . . . ?
C8 C9 O17 C10 -173.5(3) . . . . ?
C2 C1 N1 O2 47.6(5) . . . . ?
N2 C1 N1 O2 -76.2(4) . . . . ?
C2 C1 N1 O1 -127.2(4) . . . . ?
N2 C1 N1 O1 109.0(4) . . . . ?
C2 C1 N2 O4 31.6(5) . . . . ?
N1 C1 N2 O4 153.9(4) . . . . ?
C2 C1 N2 O3 -151.3(4) . . . . ?
N1 C1 N2 O3 -28.9(5) . . . . ?
C3 C2 N3 O5 0.3(4) . . . . ?
C1 C2 N3 O5 -177.2(3) . . . . ?
N4 O5 N3 C2 -0.8(4) . . . . ?
O6 C3 N4 O5 178.9(3) . . . . ?
C2 C3 N4 O5 -0.8(4) . . . . ?
N3 O5 N4 C3 1.0(4) . . . . ?
O6 C4 N5 O7 179.6(3) . . . . ?
C5 C4 N5 O7 -0.2(3) . . . . ?
N6 O7 N5 C4 0.3(3) . . . . ?
C4 C5 N6 O7 0.1(3) . . . . ?
C6 C5 N6 O7 179.5(3) . . . . ?
N5 O7 N6 C5 -0.3(3) . . . . ?
C5 C6 N7 O8 -26.0(5) . . . . ?
N8 C6 N7 O8 94.9(4) . . . . ?
C5 C6 N7 O11 154.5(5) . . . . ?
N8 C6 N7 O11 -84.6(5) . . . . ?
C5 C6 N8 O9 -58.3(4) . . . . ?
N7 C6 N8 O9 179.0(3) . . . . ?
C5 C6 N8 O10 119.3(4) . . . . ?
N7 C6 N8 O10 -3.3(5) . . . . ?
C11 C12 N9 O22 -75.8(7) . . . . ?
N10 C12 N9 O22 160.2(7) . . . . ?
C11 C12 N9 O21 101.0(5) . . . . ?
N10 C12 N9 O21 -22.9(5) . . . . ?
C11 C12 N10 O19 -8.7(4) . . . . ?
N9 C12 N10 O19 113.2(4) . . . . ?
C11 C12 N10 O20 166.1(4) . . . . ?
N9 C12 N10 O20 -72.1(4) . . . . ?
C10 C11 N11 O18 -0.5(3) . . . . ?
C12 C11 N11 O18 179.7(3) . . . . ?
N12 O18 N11 C11 0.4(4) . . . . ?
O17 C10 N12 O18 177.3(3) . . . . ?
C11 C10 N12 O18 -0.2(3) . . . . ?
N11 O18 N12 C10 -0.1(3) . . . . ?
O17 C9 N13 O16 178.2(3) . . . . ?
C8 C9 N13 O16 0.4(3) . . . . ?
N14 O16 N13 C9 0.0(3) . . . . ?
C9 C8 N14 O16 0.6(3) . . . . ?
C7 C8 N14 O16 179.0(2) . . . . ?
N13 O16 N14 C8 -0.4(3) . . . . ?
C8 C7 N15 O13 -39.2(4) . . . . ?
N16 C7 N15 O13 83.6(3) . . . . ?
C8 C7 N15 O12 139.9(3) . . . . ?
N16 C7 N15 O12 -97.4(3) . . . . ?
C8 C7 N16 O15 -33.3(4) . . . . ?
N15 C7 N16 O15 -155.9(3) . . . . ?
C8 C7 N16 O14 148.4(3) . . . . ?
N15 C7 N16 O14 25.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb7246_0m
_database_code_depnum_ccdc_archive 'CCDC 1028789'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 N14 O11'
_chemical_formula_weight         480.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8823(16)
_cell_length_b                   10.2514(18)
_cell_length_c                   10.7178(19)
_cell_angle_alpha                78.079(3)
_cell_angle_beta                 83.683(3)
_cell_angle_gamma                71.346(2)
_cell_volume                     903.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3002
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      1.74
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9446
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4558
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3202
_reflns_number_gt                2877
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0506P)²+0.3806P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.268(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09862(19) 1.13064(15) 0.13119(15) 0.0413(4) Uani 1 1 d . . .
N2 N 0.10049(19) 0.89160(15) 0.16656(15) 0.0415(4) Uani 1 1 d . . .
N3 N 0.2661(2) 1.04808(19) -0.11784(17) 0.0608(6) Uani 1 1 d . . .
N4 N 0.4856(2) 0.85604(18) -0.11008(16) 0.0514(5) Uani 1 1 d . . .
N5 N 0.63752(18) 0.57710(16) 0.02378(15) 0.0410(4) Uani 1 1 d . . .
N6 N 0.62908(19) 0.40405(16) 0.19413(16) 0.0441(4) Uani 1 1 d . . .
N7 N 0.40286(18) 0.63707(15) 0.39150(13) 0.0362(4) Uani 1 1 d . . .
N8 N 0.3342(2) 0.43510(16) 0.37035(14) 0.0411(4) Uani 1 1 d . . .
N9 N 0.1759(3) 0.16321(18) 0.51615(18) 0.0590(5) Uani 1 1 d . . .
H9A H 0.1071 0.1760 0.5790 0.071 Uiso 1 1 calc R . .
H9B H 0.1997 0.2334 0.4691 0.071 Uiso 1 1 calc R . .
N10 N 0.3495(2) 0.0180(2) 0.39515(18) 0.0629(5) Uani 1 1 d . . .
H10A H 0.3946 -0.0647 0.3787 0.075 Uiso 1 1 calc R . .
H10B H 0.3728 0.0885 0.3484 0.075 Uiso 1 1 calc R . .
N11 N 0.2087(3) -0.06934(19) 0.56307(18) 0.0613(6) Uani 1 1 d . . .
H11A H 0.1399 -0.0565 0.6259 0.074 Uiso 1 1 calc R . .
H11B H 0.2538 -0.1523 0.5472 0.074 Uiso 1 1 calc R . .
N12 N 0.8537(2) 0.65082(16) 0.26122(16) 0.0473(4) Uani 1 1 d . . .
H12A H 0.7861 0.6586 0.3253 0.057 Uiso 1 1 calc R . .
H12B H 0.8632 0.7246 0.2100 0.057 Uiso 1 1 calc R . .
N13 N 0.9278(2) 0.41416(16) 0.31974(15) 0.0446(4) Uani 1 1 d . . .
H13A H 0.9864 0.3326 0.3075 0.054 Uiso 1 1 calc R . .
H13B H 0.8595 0.4221 0.3833 0.054 Uiso 1 1 calc R . .
N14 N 1.0465(2) 0.51468(17) 0.14449(16) 0.0494(5) Uani 1 1 d . . .
H14A H 1.1053 0.4333 0.1319 0.059 Uiso 1 1 calc R . .
H14B H 1.0558 0.5886 0.0934 0.059 Uiso 1 1 calc R . .
O1 O 0.0055(2) 1.15414(16) 0.22435(16) 0.0674(5) Uani 1 1 d . . .
O2 O 0.1439(2) 1.22468(14) 0.06200(16) 0.0600(5) Uani 1 1 d . . .
O3 O 0.0431(2) 0.89104(17) 0.27628(16) 0.0716(5) Uani 1 1 d . . .
O4 O 0.1179(2) 0.79291(15) 0.11119(16) 0.0616(5) Uani 1 1 d . . .
O5 O 0.4003(2) 0.97989(17) -0.18349(15) 0.0688(5) Uani 1 1 d . . .
O6 O 0.43772(19) 0.75719(15) 0.10317(13) 0.0571(4) Uani 1 1 d . . .
O7 O 0.69976(16) 0.43650(14) 0.07634(13) 0.0461(4) Uani 1 1 d . . .
O8 O 0.3092(2) 0.66028(15) 0.48435(14) 0.0571(4) Uani 1 1 d . . .
O9 O 0.49279(17) 0.71172(14) 0.35360(13) 0.0475(4) Uani 1 1 d . . .
O10 O 0.2332(2) 0.44794(17) 0.45892(14) 0.0587(4) Uani 1 1 d . . .
O11 O 0.3649(2) 0.33538(17) 0.31501(16) 0.0661(5) Uani 1 1 d . . .
C1 C 0.1515(2) 1.00059(17) 0.09829(17) 0.0358(4) Uani 1 1 d . . .
C2 C 0.2659(2) 0.97073(18) -0.00639(17) 0.0357(4) Uani 1 1 d . . .
C3 C 0.4033(2) 0.85180(18) -0.00416(16) 0.0372(4) Uani 1 1 d . . .
C4 C 0.5319(2) 0.62462(18) 0.10838(16) 0.0346(4) Uani 1 1 d . . .
C5 C 0.5243(2) 0.51886(17) 0.21537(16) 0.0330(4) Uani 1 1 d . . .
C6 C 0.4170(2) 0.53174(17) 0.32749(16) 0.0340(4) Uani 1 1 d . . .
C7 C 0.2446(2) 0.0368(2) 0.49200(18) 0.0448(5) Uani 1 1 d . . .
C8 C 0.9426(2) 0.52611(18) 0.24163(16) 0.0335(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O2 1.236(2) . ?
N1 O1 1.237(2) . ?
N1 C1 1.371(2) . ?
N2 O3 1.229(2) . ?
N2 O4 1.236(2) . ?
N2 C1 1.379(2) . ?
N3 C2 1.290(2) . ?
N3 O5 1.375(2) . ?
N4 C3 1.281(2) . ?
N4 O5 1.381(2) . ?
N5 C4 1.282(2) . ?
N5 O7 1.387(2) . ?
N6 C5 1.291(2) . ?
N6 O7 1.373(2) . ?
N7 O8 1.2362(19) . ?
N7 O9 1.2569(19) . ?
N7 C6 1.361(2) . ?
N8 O11 1.228(2) . ?
N8 O10 1.229(2) . ?
N8 C6 1.392(2) . ?
N9 C7 1.310(3) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 C7 1.318(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 C7 1.300(3) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 C8 1.316(2) . ?
N12 H12A 0.8600 . ?
N12 H12B 0.8600 . ?
N13 C8 1.308(2) . ?
N13 H13A 0.8600 . ?
N13 H13B 0.8600 . ?
N14 C8 1.311(2) . ?
N14 H14A 0.8600 . ?
N14 H14B 0.8600 . ?
O6 C3 1.336(2) . ?
O6 C4 1.342(2) . ?
C1 C2 1.441(2) . ?
C2 C3 1.421(3) . ?
C4 C5 1.418(2) . ?
C5 C6 1.450(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 121.17(16) . . ?
O2 N1 C1 117.46(16) . . ?
O1 N1 C1 121.34(15) . . ?
O3 N2 O4 121.69(16) . . ?
O3 N2 C1 122.44(16) . . ?
O4 N2 C1 115.87(15) . . ?
C2 N3 O5 106.07(16) . . ?
C3 N4 O5 103.34(15) . . ?
C4 N5 O7 103.26(14) . . ?
C5 N6 O7 106.02(14) . . ?
O8 N7 O9 119.61(15) . . ?
O8 N7 C6 123.39(15) . . ?
O9 N7 C6 116.98(14) . . ?
O11 N8 O10 120.54(16) . . ?
O11 N8 C6 117.16(15) . . ?
O10 N8 C6 122.31(15) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C7 N10 H10A 120.0 . . ?
C7 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C7 N11 H11A 120.0 . . ?
C7 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C8 N12 H12A 120.0 . . ?
C8 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C8 N13 H13A 120.0 . . ?
C8 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C8 N14 H14A 120.0 . . ?
C8 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
N3 O5 N4 111.58(14) . . ?
C3 O6 C4 124.64(14) . . ?
N6 O7 N5 111.49(12) . . ?
N1 C1 N2 121.19(15) . . ?
N1 C1 C2 121.61(15) . . ?
N2 C1 C2 117.17(15) . . ?
N3 C2 C3 107.11(16) . . ?
N3 C2 C1 126.85(17) . . ?
C3 C2 C1 126.01(16) . . ?
N4 C3 O6 128.07(17) . . ?
N4 C3 C2 111.90(16) . . ?
O6 C3 C2 119.89(15) . . ?
N5 C4 O6 126.76(16) . . ?
N5 C4 C5 111.87(16) . . ?
O6 C4 C5 121.37(15) . . ?
N6 C5 C4 107.36(16) . . ?
N6 C5 C6 124.84(16) . . ?
C4 C5 C6 127.77(15) . . ?
N7 C6 N8 121.02(15) . . ?
N7 C6 C5 118.77(15) . . ?
N8 C6 C5 120.18(15) . . ?
N11 C7 N9 120.03(18) . . ?
N11 C7 N10 120.34(19) . . ?
N9 C7 N10 119.64(19) . . ?
N13 C8 N14 120.31(16) . . ?
N13 C8 N12 119.85(16) . . ?
N14 C8 N12 119.84(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N3 O5 N4 0.2(3) . . . . ?
C3 N4 O5 N3 0.0(2) . . . . ?
C5 N6 O7 N5 0.80(19) . . . . ?
C4 N5 O7 N6 -0.76(19) . . . . ?
O2 N1 C1 N2 -176.74(18) . . . . ?
O1 N1 C1 N2 1.2(3) . . . . ?
O2 N1 C1 C2 5.1(3) . . . . ?
O1 N1 C1 C2 -176.97(18) . . . . ?
O3 N2 C1 N1 -20.3(3) . . . . ?
O4 N2 C1 N1 160.62(18) . . . . ?
O3 N2 C1 C2 157.96(19) . . . . ?
O4 N2 C1 C2 -21.1(3) . . . . ?
O5 N3 C2 C3 -0.3(2) . . . . ?
O5 N3 C2 C1 177.77(19) . . . . ?
N1 C1 C2 N3 -44.3(3) . . . . ?
N2 C1 C2 N3 137.5(2) . . . . ?
N1 C1 C2 C3 133.4(2) . . . . ?
N2 C1 C2 C3 -44.8(3) . . . . ?
O5 N4 C3 O6 -175.8(2) . . . . ?
O5 N4 C3 C2 -0.2(2) . . . . ?
C4 O6 C3 N4 -25.6(3) . . . . ?
C4 O6 C3 C2 159.13(19) . . . . ?
N3 C2 C3 N4 0.3(2) . . . . ?
C1 C2 C3 N4 -177.76(18) . . . . ?
N3 C2 C3 O6 176.30(19) . . . . ?
C1 C2 C3 O6 -1.8(3) . . . . ?
O7 N5 C4 O6 179.55(18) . . . . ?
O7 N5 C4 C5 0.4(2) . . . . ?
C3 O6 C4 N5 21.4(3) . . . . ?
C3 O6 C4 C5 -159.60(18) . . . . ?
O7 N6 C5 C4 -0.49(19) . . . . ?
O7 N6 C5 C6 177.56(15) . . . . ?
N5 C4 C5 N6 0.0(2) . . . . ?
O6 C4 C5 N6 -179.14(18) . . . . ?
N5 C4 C5 C6 -177.95(17) . . . . ?
O6 C4 C5 C6 2.9(3) . . . . ?
O8 N7 C6 N8 -5.4(3) . . . . ?
O9 N7 C6 N8 173.45(16) . . . . ?
O8 N7 C6 C5 176.56(16) . . . . ?
O9 N7 C6 C5 -4.6(2) . . . . ?
O11 N8 C6 N7 -173.03(17) . . . . ?
O10 N8 C6 N7 7.6(3) . . . . ?
O11 N8 C6 C5 5.0(3) . . . . ?
O10 N8 C6 C5 -174.39(17) . . . . ?
N6 C5 C6 N7 131.43(19) . . . . ?
C4 C5 C6 N7 -50.9(3) . . . . ?
N6 C5 C6 N8 -46.6(3) . . . . ?
C4 C5 C6 N8 131.02(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1041345'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H8 N9 O5.50'
_chemical_formula_weight         283.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   13.873(9)
_cell_length_b                   11.275(7)
_cell_length_c                   14.334(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2242(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9471
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12138
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2000
_reflns_number_gt                1396
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0945P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2000
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36742(18) 1.0839(2) 0.15557(18) 0.0379(7) Uani 1 1 d . . .
N2 N 0.38520(19) 1.0224(2) -0.00510(19) 0.0399(7) Uani 1 1 d . . .
N3 N 0.3315(2) 0.7904(2) 0.0794(2) 0.0576(9) Uani 1 1 d . . .
N4 N 0.4229(2) 0.7038(2) 0.1935(2) 0.0567(9) Uani 1 1 d . . .
N5 N 0.1291(2) 0.0607(2) 0.7497(2) 0.0511(8) Uani 1 1 d . . .
H5A H 0.1384 0.1083 0.7036 0.061 Uiso 1 1 calc R . .
H5B H 0.1316 -0.0147 0.7410 0.061 Uiso 1 1 calc R . .
N6 N 0.1079(2) 0.2208(2) 0.8443(2) 0.0503(8) Uani 1 1 d . . .
H6A H 0.1174 0.2661 0.7970 0.060 Uiso 1 1 calc R . .
H6B H 0.0964 0.2512 0.8982 0.060 Uiso 1 1 calc R . .
N7 N 0.09043(18) 0.0393(2) 0.90977(19) 0.0402(7) Uani 1 1 d . . .
N8 N 0.0817(2) -0.1315(2) 0.9923(2) 0.0567(9) Uani 1 1 d . . .
H8A H 0.1030 -0.2006 1.0072 0.068 Uiso 1 1 calc R . .
H8B H 0.0324 -0.1026 1.0205 0.068 Uiso 1 1 calc R . .
N9 N 0.2012(2) -0.1173(2) 0.8835(2) 0.0514(8) Uani 1 1 d . . .
H9A H 0.2214 -0.1865 0.8995 0.062 Uiso 1 1 calc R . .
H9B H 0.2304 -0.0787 0.8402 0.062 Uiso 1 1 calc R . .
O1 O 0.35087(18) 1.0503(2) 0.23796(17) 0.0544(7) Uani 1 1 d . . .
O2 O 0.37777(18) 1.19139(19) 0.13728(18) 0.0533(7) Uani 1 1 d . . .
O3 O 0.3623(2) 1.1205(2) -0.03697(18) 0.0694(9) Uani 1 1 d . . .
O4 O 0.41530(17) 0.94225(18) -0.05716(16) 0.0501(7) Uani 1 1 d . . .
O5 O 0.3557(2) 0.6854(2) 0.1222(2) 0.0698(9) Uani 1 1 d . . .
O6 O 0.5000 0.8761(2) 0.2500 0.0441(8) Uani 1 2 d S . .
C1 C 0.3764(2) 0.9962(2) 0.0902(2) 0.0340(7) Uani 1 1 d . . .
C2 C 0.3815(2) 0.8731(3) 0.1211(2) 0.0379(8) Uani 1 1 d . . .
C3 C 0.4388(2) 0.8167(2) 0.1926(2) 0.0398(8) Uani 1 1 d . . .
C4 C 0.11104(19) 0.1037(3) 0.8342(2) 0.0328(7) Uani 1 1 d . . .
C5 C 0.1249(2) -0.0699(3) 0.9260(2) 0.0388(8) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O2 1.249(3) . ?
N1 O1 1.261(4) . ?
N1 C1 1.368(4) . ?
N2 O3 1.238(3) . ?
N2 O4 1.245(3) . ?
N2 C1 1.403(4) . ?
N3 C2 1.307(4) . ?
N3 O5 1.374(4) . ?
N4 C3 1.291(4) . ?
N4 O5 1.399(4) . ?
N5 C4 1.330(4) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 C4 1.328(4) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 C4 1.335(4) . ?
N7 C5 1.341(4) . ?
N8 C5 1.321(4) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 C5 1.334(4) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
O6 C3 1.359(3) 3_655 ?
O6 C3 1.359(3) . ?
C1 C2 1.459(4) . ?
C2 C3 1.444(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 120.6(3) . . ?
O2 N1 C1 123.2(3) . . ?
O1 N1 C1 116.1(3) . . ?
O3 N2 O4 120.9(3) . . ?
O3 N2 C1 121.7(3) . . ?
O4 N2 C1 117.4(3) . . ?
C2 N3 O5 106.3(3) . . ?
C3 N4 O5 104.6(3) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C4 N6 H6A 120.0 . . ?
C4 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C4 N7 C5 124.3(3) . . ?
C5 N8 H8A 120.0 . . ?
C5 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C5 N9 H9A 120.0 . . ?
C5 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
N3 O5 N4 111.2(2) . . ?
C3 O6 C3 120.9(3) 3_655 . ?
N1 C1 N2 121.5(3) . . ?
N1 C1 C2 118.9(3) . . ?
N2 C1 C2 119.5(3) . . ?
N3 C2 C3 107.6(3) . . ?
N3 C2 C1 120.9(3) . . ?
C3 C2 C1 131.4(3) . . ?
N4 C3 O6 125.9(3) . . ?
N4 C3 C2 110.3(3) . . ?
O6 C3 C2 123.8(3) . . ?
N6 C4 N5 117.9(3) . . ?
N6 C4 N7 116.4(3) . . ?
N5 C4 N7 125.6(3) . . ?
N8 C5 N9 118.5(3) . . ?
N8 C5 N7 116.5(3) . . ?
N9 C5 N7 124.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N3 O5 N4 0.3(4) . . . . ?
C3 N4 O5 N3 -0.4(4) . . . . ?
O2 N1 C1 N2 -8.7(4) . . . . ?
O1 N1 C1 N2 173.5(2) . . . . ?
O2 N1 C1 C2 168.3(3) . . . . ?
O1 N1 C1 C2 -9.5(4) . . . . ?
O3 N2 C1 N1 -17.9(4) . . . . ?
O4 N2 C1 N1 163.5(3) . . . . ?
O3 N2 C1 C2 165.1(3) . . . . ?
O4 N2 C1 C2 -13.4(4) . . . . ?
O5 N3 C2 C3 -0.1(4) . . . . ?
O5 N3 C2 C1 177.3(3) . . . . ?
N1 C1 C2 N3 135.1(3) . . . . ?
N2 C1 C2 N3 -47.8(4) . . . . ?
N1 C1 C2 C3 -48.1(5) . . . . ?
N2 C1 C2 C3 128.9(4) . . . . ?
O5 N4 C3 O6 -179.7(3) . . . . ?
O5 N4 C3 C2 0.3(4) . . . . ?
C3 O6 C3 N4 8.9(3) 3_655 . . . ?
C3 O6 C3 C2 -171.2(4) 3_655 . . . ?
N3 C2 C3 N4 -0.2(4) . . . . ?
C1 C2 C3 N4 -177.2(3) . . . . ?
N3 C2 C3 O6 179.9(3) . . . . ?
C1 C2 C3 O6 2.8(5) . . . . ?
C5 N7 C4 N6 -152.2(3) . . . . ?
C5 N7 C4 N5 31.6(5) . . . . ?
C4 N7 C5 N8 -165.5(3) . . . . ?
C4 N7 C5 N9 17.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.246
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb8035_0m
_database_code_depnum_ccdc_archive 'CCDC 1041566'
_audit_update_record             
;
2015-01-05 deposited with the CCDC.
2015-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H8 N10 O11'
_chemical_formula_weight         396.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.691(4)
_cell_length_b                   9.290(5)
_cell_length_c                   10.564(5)
_cell_angle_alpha                94.504(8)
_cell_angle_beta                 104.174(7)
_cell_angle_gamma                100.366(7)
_cell_volume                     713.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2050
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9383
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3575
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2513
_reflns_number_gt                2221
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.037(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2513
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7561(2) 1.00177(18) 0.51679(16) 0.0314(4) Uani 1 1 d . . .
N2 N 0.6157(2) 1.20676(18) 0.45074(16) 0.0322(4) Uani 1 1 d . . .
N3 N 0.8665(2) 1.1606(2) 0.26197(17) 0.0400(4) Uani 1 1 d . . .
N4 N 0.7017(2) 0.98747(19) 0.08741(16) 0.0336(4) Uani 1 1 d . . .
N5 N 0.4799(2) 0.71787(19) -0.00331(16) 0.0378(4) Uani 1 1 d . . .
N6 N 0.2242(2) 0.5479(2) -0.00629(19) 0.0464(5) Uani 1 1 d . . .
N7 N 0.0261(2) 0.74049(17) 0.17726(15) 0.0306(4) Uani 1 1 d . . .
N8 N 0.1530(2) 0.54537(18) 0.27782(17) 0.0341(4) Uani 1 1 d . . .
N9 N 0.2799(3) 0.4098(2) 0.5764(2) 0.0444(5) Uani 1 1 d . . .
N10 N 0.2344(3) 0.1721(2) 0.15508(19) 0.0373(4) Uani 1 1 d . . .
O1 O 0.7339(2) 1.01468(17) 0.62892(13) 0.0457(4) Uani 1 1 d . . .
O2 O 0.8210(2) 0.90061(16) 0.47573(15) 0.0431(4) Uani 1 1 d . . .
O3 O 0.5758(2) 1.23158(18) 0.55628(15) 0.0462(4) Uani 1 1 d . . .
O4 O 0.5669(2) 1.27917(16) 0.35617(16) 0.0459(4) Uani 1 1 d . . .
O5 O 0.84563(19) 1.10926(17) 0.13184(14) 0.0422(4) Uani 1 1 d . . .
O6 O 0.49445(19) 0.86415(16) 0.19365(13) 0.0412(4) Uani 1 1 d . . .
O7 O 0.3580(2) 0.59014(18) -0.06951(15) 0.0485(4) Uani 1 1 d . . .
O8 O -0.0881(2) 0.74055(19) 0.24032(16) 0.0467(4) Uani 1 1 d . . .
O9 O 0.0457(2) 0.83166(17) 0.09742(14) 0.0413(4) Uani 1 1 d . . .
O10 O 0.0578(2) 0.53693(19) 0.35731(17) 0.0489(4) Uani 1 1 d . . .
O11 O 0.2705(2) 0.46570(17) 0.28154(16) 0.0487(4) Uani 1 1 d . . .
C1 C 0.7090(2) 1.1003(2) 0.42790(18) 0.0288(4) Uani 1 1 d . . .
C2 C 0.7395(2) 1.0754(2) 0.29844(18) 0.0290(4) Uani 1 1 d . . .
C3 C 0.6394(2) 0.9681(2) 0.18829(18) 0.0287(4) Uani 1 1 d . . .
C4 C 0.4200(2) 0.7502(2) 0.09711(18) 0.0299(4) Uani 1 1 d . . .
C5 C 0.2590(2) 0.6459(2) 0.09655(18) 0.0298(4) Uani 1 1 d . . .
C6 C 0.1423(2) 0.6421(2) 0.18676(18) 0.0283(4) Uani 1 1 d . . .
H9A H 0.210(5) 0.415(4) 0.492(4) 0.072(9) Uiso 1 1 d . . .
H9B H 0.352(6) 0.506(6) 0.596(4) 0.114(14) Uiso 1 1 d . . .
H9C H 0.198(5) 0.390(4) 0.627(3) 0.077(10) Uiso 1 1 d . . .
H9D H 0.339(6) 0.328(6) 0.567(4) 0.129(16) Uiso 1 1 d . . .
H10D H 0.206(5) 0.091(5) 0.210(4) 0.107(12) Uiso 1 1 d . . .
H10C H 0.333(5) 0.172(4) 0.126(3) 0.093(12) Uiso 1 1 d . . .
H10B H 0.245(6) 0.275(6) 0.190(4) 0.117(14) Uiso 1 1 d . . .
H10A H 0.143(9) 0.176(7) 0.099(6) 0.17(2) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.237(2) . ?
N1 O2 1.237(2) . ?
N1 C1 1.392(3) . ?
N2 O3 1.242(2) . ?
N2 O4 1.267(2) . ?
N2 C1 1.361(3) . ?
N3 C2 1.297(2) . ?
N3 O5 1.380(2) . ?
N4 C3 1.283(2) . ?
N4 O5 1.392(2) . ?
N5 C4 1.291(2) . ?
N5 O7 1.387(2) . ?
N6 C5 1.302(3) . ?
N6 O7 1.376(2) . ?
N7 O8 1.226(2) . ?
N7 O9 1.257(2) . ?
N7 C6 1.381(3) . ?
N8 O10 1.240(2) . ?
N8 O11 1.263(2) . ?
N8 C6 1.365(3) . ?
N9 H9A 0.93(4) . ?
N9 H9B 0.94(5) . ?
N9 H9C 0.92(4) . ?
N9 H9D 0.96(5) . ?
N10 H10D 1.01(4) . ?
N10 H10C 0.88(4) . ?
N10 H10B 0.98(5) . ?
N10 H10A 0.81(6) . ?
O6 C4 1.347(2) . ?
O6 C3 1.353(2) . ?
C1 C2 1.451(3) . ?
C2 C3 1.430(3) . ?
C4 C5 1.427(3) . ?
C5 C6 1.459(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 122.50(16) . . ?
O1 N1 C1 122.11(17) . . ?
O2 N1 C1 115.40(16) . . ?
O3 N2 O4 120.74(16) . . ?
O3 N2 C1 123.14(16) . . ?
O4 N2 C1 116.10(16) . . ?
C2 N3 O5 105.77(16) . . ?
C3 N4 O5 103.68(15) . . ?
C4 N5 O7 104.01(15) . . ?
C5 N6 O7 106.09(17) . . ?
O8 N7 O9 121.74(16) . . ?
O8 N7 C6 123.71(16) . . ?
O9 N7 C6 114.55(15) . . ?
O10 N8 O11 120.09(16) . . ?
O10 N8 C6 122.98(16) . . ?
O11 N8 C6 116.89(17) . . ?
H9A N9 H9B 100(3) . . ?
H9A N9 H9C 106(3) . . ?
H9B N9 H9C 115(3) . . ?
H9A N9 H9D 105(3) . . ?
H9B N9 H9D 118(4) . . ?
H9C N9 H9D 111(3) . . ?
H10D N10 H10C 115(3) . . ?
H10D N10 H10B 119(3) . . ?
H10C N10 H10B 105(3) . . ?
H10D N10 H10A 110(5) . . ?
H10C N10 H10A 115(4) . . ?
H10B N10 H10A 90(4) . . ?
N3 O5 N4 111.51(13) . . ?
C4 O6 C3 121.33(15) . . ?
N6 O7 N5 111.37(15) . . ?
N2 C1 N1 123.02(17) . . ?
N2 C1 C2 118.48(16) . . ?
N1 C1 C2 117.98(17) . . ?
N3 C2 C3 107.59(17) . . ?
N3 C2 C1 122.35(17) . . ?
C3 C2 C1 129.95(16) . . ?
N4 C3 O6 126.32(17) . . ?
N4 C3 C2 111.45(16) . . ?
O6 C3 C2 122.20(16) . . ?
N5 C4 O6 126.99(17) . . ?
N5 C4 C5 111.07(17) . . ?
O6 C4 C5 121.93(16) . . ?
N6 C5 C4 107.45(17) . . ?
N6 C5 C6 122.59(17) . . ?
C4 C5 C6 129.93(17) . . ?
N8 C6 N7 122.50(17) . . ?
N8 C6 C5 119.87(17) . . ?
N7 C6 C5 117.61(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N3 O5 N4 -0.5(2) . . . . ?
C3 N4 O5 N3 0.19(19) . . . . ?
C5 N6 O7 N5 0.3(2) . . . . ?
C4 N5 O7 N6 0.3(2) . . . . ?
O3 N2 C1 N1 5.1(3) . . . . ?
O4 N2 C1 N1 -173.45(16) . . . . ?
O3 N2 C1 C2 176.66(16) . . . . ?
O4 N2 C1 C2 -1.9(2) . . . . ?
O1 N1 C1 N2 -8.1(3) . . . . ?
O2 N1 C1 N2 171.70(17) . . . . ?
O1 N1 C1 C2 -179.72(16) . . . . ?
O2 N1 C1 C2 0.1(2) . . . . ?
O5 N3 C2 C3 0.6(2) . . . . ?
O5 N3 C2 C1 -175.90(16) . . . . ?
N2 C1 C2 N3 78.6(2) . . . . ?
N1 C1 C2 N3 -109.4(2) . . . . ?
N2 C1 C2 C3 -97.0(2) . . . . ?
N1 C1 C2 C3 75.0(2) . . . . ?
O5 N4 C3 O6 178.17(17) . . . . ?
O5 N4 C3 C2 0.19(19) . . . . ?
C4 O6 C3 N4 12.9(3) . . . . ?
C4 O6 C3 C2 -169.34(17) . . . . ?
N3 C2 C3 N4 -0.5(2) . . . . ?
C1 C2 C3 N4 175.62(18) . . . . ?
N3 C2 C3 O6 -178.61(17) . . . . ?
C1 C2 C3 O6 -2.5(3) . . . . ?
O7 N5 C4 O6 178.53(18) . . . . ?
O7 N5 C4 C5 -0.7(2) . . . . ?
C3 O6 C4 N5 5.6(3) . . . . ?
C3 O6 C4 C5 -175.27(17) . . . . ?
O7 N6 C5 C4 -0.7(2) . . . . ?
O7 N6 C5 C6 177.70(17) . . . . ?
N5 C4 C5 N6 0.9(2) . . . . ?
O6 C4 C5 N6 -178.35(18) . . . . ?
N5 C4 C5 C6 -177.32(19) . . . . ?
O6 C4 C5 C6 3.4(3) . . . . ?
O10 N8 C6 N7 1.1(3) . . . . ?
O11 N8 C6 N7 -176.62(16) . . . . ?
O10 N8 C6 C5 179.89(17) . . . . ?
O11 N8 C6 C5 2.2(3) . . . . ?
O8 N7 C6 N8 -7.0(3) . . . . ?
O9 N7 C6 N8 173.23(16) . . . . ?
O8 N7 C6 C5 174.22(17) . . . . ?
O9 N7 C6 C5 -5.6(2) . . . . ?
N6 C5 C6 N8 77.8(3) . . . . ?
C4 C5 C6 N8 -104.2(2) . . . . ?
N6 C5 C6 N7 -103.4(2) . . . . ?
C4 C5 C6 N7 74.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.052
